So my first batch of venture investments hit 20x this week

I'd like to say the learnings are novel or different than others

But they aren't

Learnings:

1. All that matters are the winners

The #1 investment is 55% of the returns

The #2 and #3 are each 12%.

So Top 3 = 79%

2. Yes, ownership matters.

Of course 2% of Zoom and Datadog are plenty for all but the largest funds.

But, the winners with the most ownership, have the biggest returns.

Just as you'd expect.

3. Double down on the winners, skip the rest.

You hear this, but then you see it in practice. Do you pro-rata on your Top 3 investments, at any price.

Skip it on the rest after the next round, probably, unless it supports the investment.

4. Somewhat More Investments is simply better.

Concentrated strategy ftw. But ... passing on one with a ton of positives never helps.

Just do any investment ... that truly meets your high bar.

Worst case, you lose a little.

5. All of the top investments were strong when I invested. BUT -- they all went on to have 1 bad year. A bad one.

They got through it. So can you. More here: https://www.saastr.com/the-saas-year-of-hell-and-then-reignition/t

6. A Big TAM does help. Most of the top investments had a huge TAM, in an existing, large category. But some had tiny TAMs (<$10m).

A tiny TAM is OK. You can grow it. See, e.g. Airbnb where it started and where it is today.

But it does help to start with a $100B+ category.

7. Agile FTW. Most of the top investments had to > completely< rebuild their products. That's hard. You can do it completely, or you can build up to it as you add more and more features.

But if you don't have a truly agile team, you get left behind.

8. The Best CEOs Can Take the Constructive Criticism. The rest can't.

More a meta-learning, but I try to hold my tongue after $10m ARR, and am going to keep to it.

But I've learned the best CEOs seek out challenges. The rest though -- take it personally.

Don't invest there.